JP2014517833A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014517833A5 JP2014517833A5 JP2014510414A JP2014510414A JP2014517833A5 JP 2014517833 A5 JP2014517833 A5 JP 2014517833A5 JP 2014510414 A JP2014510414 A JP 2014510414A JP 2014510414 A JP2014510414 A JP 2014510414A JP 2014517833 A5 JP2014517833 A5 JP 2014517833A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroaryl
- aryl
- cycloalkyl
- heterocyclyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000001072 heteroaryl group Chemical group 0.000 claims description 122
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 56
- -1 -N (R 26 ) (R 28 ) Chemical group 0.000 claims description 48
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- GXKPZKOLTOGOTN-UHFFFAOYSA-N 2,2-dimethyl-3-(pyridin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazin-4-one Chemical compound CC1(C)OC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC1=CC=CC=N1 GXKPZKOLTOGOTN-UHFFFAOYSA-N 0.000 claims description 2
- IRDRGAPMRVUDIT-UHFFFAOYSA-N 2-methyl-3-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-2h-1,3-benzoxazin-4-one Chemical compound CC1OC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC1=NC=CC=N1 IRDRGAPMRVUDIT-UHFFFAOYSA-N 0.000 claims description 2
- LKIWLRFRMTVENN-UHFFFAOYSA-N 3-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-2h-1,3-benzoxazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCN(CC=2N=CC=CN=2)C2=O)C2=C1 LKIWLRFRMTVENN-UHFFFAOYSA-N 0.000 claims description 2
- SUYKISAGQQPNCL-UHFFFAOYSA-N 3-benzyl-6-[2-fluoro-4-(trifluoromethyl)phenyl]-2H-1,3-benzoxazin-4-one 3-benzyl-6-[4-(trifluoromethyl)phenyl]-2H-1,3-benzoxazin-4-one Chemical compound FC(F)(F)c1ccc(cc1)-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1.Fc1cc(ccc1-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1)C(F)(F)F SUYKISAGQQPNCL-UHFFFAOYSA-N 0.000 claims description 2
- SOIWRRAHACEUQO-UHFFFAOYSA-N 6-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(pyrimidin-2-ylmethyl)-2h-1,3-benzoxazin-4-one Chemical compound FC1=CC(C(F)(F)F)=CC=C1C1=CC=C(OCN(CC=2N=CC=CN=2)C2=O)C2=C1 SOIWRRAHACEUQO-UHFFFAOYSA-N 0.000 claims description 2
- RKZMXFKGMJTFTP-UHFFFAOYSA-N N1=C(C=CC=C1)CN1COC2=C(C1=O)C=C(C=C2)C2=CC=C(C=C2)OC(F)(F)F.N2=C(C=CC=C2)CN2COC1=C(C2=O)C=C(C=C1)C1=CC=C(C=C1)C(F)(F)F Chemical compound N1=C(C=CC=C1)CN1COC2=C(C1=O)C=C(C=C2)C2=CC=C(C=C2)OC(F)(F)F.N2=C(C=CC=C2)CN2COC1=C(C2=O)C=C(C=C1)C1=CC=C(C=C1)C(F)(F)F RKZMXFKGMJTFTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000001568 sexual effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 206010007559 Cardiac failure congestive Diseases 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- OKCXFMIRAGPOBE-UHFFFAOYSA-N (1,3-dimethylpyrazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound CC1=NN(C)C=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OKCXFMIRAGPOBE-UHFFFAOYSA-N 0.000 description 1
- OMYBLTTTXLCPBJ-UHFFFAOYSA-N (1-methylimidazol-2-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound CN1C=CN=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OMYBLTTTXLCPBJ-UHFFFAOYSA-N 0.000 description 1
- DMUHWIXKAPTSAU-UHFFFAOYSA-N (1-propan-2-ylpyrazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=NN(C(C)C)C=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 DMUHWIXKAPTSAU-UHFFFAOYSA-N 0.000 description 1
- QMJVNJAJVGDCTL-UHFFFAOYSA-N (2-amino-6-methylpyrimidin-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound NC1=NC(C)=CC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 QMJVNJAJVGDCTL-UHFFFAOYSA-N 0.000 description 1
- ACZIDEGROKLYPO-UHFFFAOYSA-N (2-propan-2-ylpyrimidin-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound CC(C)C1=NC=CC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 ACZIDEGROKLYPO-UHFFFAOYSA-N 0.000 description 1
- UKVNDDGLEBQGAQ-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)N3CC(F)(F)C3)C2=C1 UKVNDDGLEBQGAQ-UHFFFAOYSA-N 0.000 description 1
- YWTSRZSAIBLJJD-UHFFFAOYSA-N (3-amino-1h-1,2,4-triazol-5-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound NC1=NNC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 YWTSRZSAIBLJJD-UHFFFAOYSA-N 0.000 description 1
- GLDISGMVFCOFDU-UHFFFAOYSA-N (3-fluoroazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(F)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GLDISGMVFCOFDU-UHFFFAOYSA-N 0.000 description 1
- FPKUCEXGARYZEA-UHFFFAOYSA-N (3-fluoropyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(F)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 FPKUCEXGARYZEA-UHFFFAOYSA-N 0.000 description 1
- ASHRRFLJDQKIRC-UHFFFAOYSA-N (3-hydroxy-3-methylazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(C)(O)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 ASHRRFLJDQKIRC-UHFFFAOYSA-N 0.000 description 1
- JSKYYSCMMKTJOE-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(O)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 JSKYYSCMMKTJOE-UHFFFAOYSA-N 0.000 description 1
- OKHGEGPMRVXEHW-UHFFFAOYSA-N (3-hydroxypyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(O)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OKHGEGPMRVXEHW-UHFFFAOYSA-N 0.000 description 1
- GYUOAYKNYKPAEL-UHFFFAOYSA-N (3-methylimidazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound CN1C=NC=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GYUOAYKNYKPAEL-UHFFFAOYSA-N 0.000 description 1
- GJTKRZUDGOBUKW-UHFFFAOYSA-N (3-methylpyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(C)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GJTKRZUDGOBUKW-UHFFFAOYSA-N 0.000 description 1
- GKKVGDDVZPXUKK-UHFFFAOYSA-N (3-methylsulfonylazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(S(=O)(=O)C)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GKKVGDDVZPXUKK-UHFFFAOYSA-N 0.000 description 1
- NJLITTFSPDEQJF-UHFFFAOYSA-N (3-pyridin-3-yloxyazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)N3CC(C3)OC=3C=NC=CC=3)C2=C1 NJLITTFSPDEQJF-UHFFFAOYSA-N 0.000 description 1
- FPRIKTQPYWSEMF-UHFFFAOYSA-N 1-[4-[4-oxo-3-(2-pyrimidin-2-yloxyethyl)-1,2,3-benzotriazin-6-yl]phenyl]cyclopropane-1-carbonitrile Chemical compound N1=NC2=CC=C(C=3C=CC(=CC=3)C3(CC3)C#N)C=C2C(=O)N1CCOC1=NC=CC=N1 FPRIKTQPYWSEMF-UHFFFAOYSA-N 0.000 description 1
- AISSCWTVTWYJLD-UHFFFAOYSA-N 1-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]cyclopropane-1-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(C2=O)C3(CC3)C#N)C2=C1 AISSCWTVTWYJLD-UHFFFAOYSA-N 0.000 description 1
- ZMTOTPBCIRSDAD-UHFFFAOYSA-N 1h-imidazol-2-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3NC=CN=3)C2=C1 ZMTOTPBCIRSDAD-UHFFFAOYSA-N 0.000 description 1
- DPTITYSAZQWYGL-UHFFFAOYSA-N 1h-pyrazol-5-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3NN=CC=3)C2=C1 DPTITYSAZQWYGL-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- YKXANQXQHPAABH-UHFFFAOYSA-N 2-(1-methylimidazol-4-yl)sulfonyl-7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinoline Chemical compound CN1C=NC(S(=O)(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1 YKXANQXQHPAABH-UHFFFAOYSA-N 0.000 description 1
- WODBRDZPPBUNAC-UHFFFAOYSA-N 2-(2-pyrazin-2-yloxyethyl)-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one 2-(2-pyridin-2-yloxyethyl)-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N1=C(C=CC=C1)OCCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O.N1=C(C=NC=C1)OCCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O WODBRDZPPBUNAC-UHFFFAOYSA-N 0.000 description 1
- XXKVWUOUIJPXIM-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethyl)-7-[2-[4-(trifluoromethyl)phenyl]ethynyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C#CC1=CC=C(CCN(CC=2N=CC=CN=2)C2=O)C2=C1 XXKVWUOUIJPXIM-UHFFFAOYSA-N 0.000 description 1
- YNGZSMBCTUWODU-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(CC=2N=CC=CN=2)C2=O)C2=C1 YNGZSMBCTUWODU-UHFFFAOYSA-N 0.000 description 1
- BZHUWNKCGIIRMA-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3C=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 BZHUWNKCGIIRMA-UHFFFAOYSA-N 0.000 description 1
- CEDFXPQRXCHUDD-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one 2-[2-(6-methylpyridin-2-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound COC1=NC(=NC(=C1)OC)CN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O.CC1=CC=CC(=N1)CCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O CEDFXPQRXCHUDD-UHFFFAOYSA-N 0.000 description 1
- QJYIRGGTCVQALQ-UHFFFAOYSA-N 2-[(4-cyclopropylpyrimidin-2-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC=2N=C(C=CN=2)C2CC2)C2=O)C2=C1 QJYIRGGTCVQALQ-UHFFFAOYSA-N 0.000 description 1
- GAIWIJWVSPMLSG-UHFFFAOYSA-N 2-[(5-pyridin-2-yl-1,2-oxazol-3-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC2=NOC(=C2)C=2N=CC=CC=2)C2=O)C2=C1 GAIWIJWVSPMLSG-UHFFFAOYSA-N 0.000 description 1
- LSXVROBUHDBFTR-UHFFFAOYSA-N 2-[2-(1,2,4-triazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CCN2N=CN=C2)C2=O)C2=C1 LSXVROBUHDBFTR-UHFFFAOYSA-N 0.000 description 1
- CHRJXNABLDTLAB-UHFFFAOYSA-N 2-[2-(1-methylbenzimidazol-2-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N=1C2=CC=CC=C2N(C)C=1CCN(C(C1=C2)=O)N=CC1=CC=C2C1=CC=C(OC(F)(F)F)C=C1 CHRJXNABLDTLAB-UHFFFAOYSA-N 0.000 description 1
- ZDYYRTGGVZVNQK-UHFFFAOYSA-N 2-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N1=C(C)C=C(C)N1CCN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2C=N1 ZDYYRTGGVZVNQK-UHFFFAOYSA-N 0.000 description 1
- FZWHXZRUTBUZEW-UHFFFAOYSA-N 2-[2-(5-methylpyrazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound CC1=CC=NN1CCN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2C=N1 FZWHXZRUTBUZEW-UHFFFAOYSA-N 0.000 description 1
- PHUULIXZSQFUMZ-UHFFFAOYSA-N 2-[2-[4-(2-methoxypyrimidin-5-yl)pyrazol-1-yl]ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=NC(OC)=NC=C1C1=CN(CCN2C(C3=CC(=CC=C3C=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)N=C1 PHUULIXZSQFUMZ-UHFFFAOYSA-N 0.000 description 1
- VWESYXQKYFUHHT-UHFFFAOYSA-N 2-[2-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]ethoxy]pyrimidine-4-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=C(C=CN=2)C#N)C2=O)C2=C1 VWESYXQKYFUHHT-UHFFFAOYSA-N 0.000 description 1
- RHDGAKMQPCICPN-UHFFFAOYSA-N 2-[2-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]ethoxy]pyrimidine-5-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=CC(=CN=2)C#N)C2=O)C2=C1 RHDGAKMQPCICPN-UHFFFAOYSA-N 0.000 description 1
- ZSIVVPXRCFYFJK-UHFFFAOYSA-N 2-[4-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]triazol-1-yl]acetic acid Chemical compound OC(=O)Cn1cc(nn1)C(=O)N1CCc2ccc(cc2C1)-c1ccc(cc1)C(F)(F)F ZSIVVPXRCFYFJK-UHFFFAOYSA-N 0.000 description 1
- FRBXKOSFLJXJLT-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyrimidin-2-yl]methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC=2N=C(OCC3CC3)C=CN=2)C2=O)C2=C1 FRBXKOSFLJXJLT-UHFFFAOYSA-N 0.000 description 1
- YQACCKXKBZZMLX-UHFFFAOYSA-N 2-pyridin-2-yl-1-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)CC=3N=CC=CC=3)C2=C1 YQACCKXKBZZMLX-UHFFFAOYSA-N 0.000 description 1
- UJYYAQCABPLOHM-UHFFFAOYSA-N 2-pyrimidin-2-yl-1-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)CC=3N=CC=CN=3)C2=C1 UJYYAQCABPLOHM-UHFFFAOYSA-N 0.000 description 1
- UQMIMGRSZZMLSM-UHFFFAOYSA-N 3-(1-pyrimidin-2-ylpiperidin-4-yl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(C2CCN(CC2)C=2N=CC=CN=2)C2=O)C2=C1 UQMIMGRSZZMLSM-UHFFFAOYSA-N 0.000 description 1
- JZFLUMILLHCMBG-UHFFFAOYSA-N 3-(2,2-dimethyl-3-pyrimidin-2-yloxypropyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound N1=NC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC(C)(C)COC1=NC=CC=N1 JZFLUMILLHCMBG-UHFFFAOYSA-N 0.000 description 1
- QVVPXWIRZIFXHG-UHFFFAOYSA-N 3-(2-pyrazol-1-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCN2N=CC=C2)C2=O)C2=C1 QVVPXWIRZIFXHG-UHFFFAOYSA-N 0.000 description 1
- KSWSXOQZMIJLFG-UHFFFAOYSA-N 3-(2-pyridin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCC=2N=CC=CC=2)C2=O)C2=C1 KSWSXOQZMIJLFG-UHFFFAOYSA-N 0.000 description 1
- ZZTNIKXOKLTCLM-UHFFFAOYSA-N 3-(2-pyrimidin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCC=2N=CC=CN=2)C2=O)C2=C1 ZZTNIKXOKLTCLM-UHFFFAOYSA-N 0.000 description 1
- UCGDXGAPXVUFBS-UHFFFAOYSA-N 3-(2-pyrimidin-2-yloxyethyl)-6-[2-[4-(trifluoromethoxy)phenyl]ethynyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C#CC1=CC=C(N=NN(CCOC=2N=CC=CN=2)C2=O)C2=C1 UCGDXGAPXVUFBS-UHFFFAOYSA-N 0.000 description 1
- BLGREARZINOIPN-UHFFFAOYSA-N 3-(2-pyrimidin-2-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=CC=CN=2)C2=O)C2=C1 BLGREARZINOIPN-UHFFFAOYSA-N 0.000 description 1
- KFDLVTFQXVLIOA-UHFFFAOYSA-N 3-(2-pyrimidin-2-yloxyethyl)-6-[6-(trifluoromethyl)pyridin-3-yl]-1,2,3-benzotriazin-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=CC=CN=2)C2=O)C2=C1 KFDLVTFQXVLIOA-UHFFFAOYSA-N 0.000 description 1
- LGZZSZBHEBUCJP-UHFFFAOYSA-N 3-(2-pyrimidin-4-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCC=2N=CN=CC=2)C2=O)C2=C1 LGZZSZBHEBUCJP-UHFFFAOYSA-N 0.000 description 1
- ZNYCMYNFOACBNK-UHFFFAOYSA-N 3-(benzotriazol-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CN2N=C3C=CC=CC3=N2)C2=O)C2=C1 ZNYCMYNFOACBNK-UHFFFAOYSA-N 0.000 description 1
- DAZDFKBNNBIFFR-UHFFFAOYSA-N 3-(pyridin-3-ylmethoxy)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(OCC=2C=NC=CC=2)C2=O)C2=C1 DAZDFKBNNBIFFR-UHFFFAOYSA-N 0.000 description 1
- RMHUZTFIZINNOW-UHFFFAOYSA-N 3-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2N=CC=CN=2)C2=O)C2=C1 RMHUZTFIZINNOW-UHFFFAOYSA-N 0.000 description 1
- QQJLJIVXERYAGI-UHFFFAOYSA-N 3-[(2-cyclobutyl-1,3-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2N=C(OC=2)C2CCC2)C2=O)C2=C1 QQJLJIVXERYAGI-UHFFFAOYSA-N 0.000 description 1
- NBRJCGZMFHTYQN-UHFFFAOYSA-N 3-[(2-methyl-1,3-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=NC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=C1 NBRJCGZMFHTYQN-UHFFFAOYSA-N 0.000 description 1
- DQWKSXVQEIDFLA-UHFFFAOYSA-N 3-[(2-methyl-1,3-oxazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=NC=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N=N1 DQWKSXVQEIDFLA-UHFFFAOYSA-N 0.000 description 1
- OCOSSKVPOKLZBP-UHFFFAOYSA-N 3-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2ON=C(CC=3C=CC=CC=3)N=2)C2=O)C2=C1 OCOSSKVPOKLZBP-UHFFFAOYSA-N 0.000 description 1
- YJYQPDPFGPKSKO-UHFFFAOYSA-N 3-[(3-fluoropyridin-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-2h-1,3-benzothiazin-4-one Chemical compound FC1=CC=CN=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2SC1 YJYQPDPFGPKSKO-UHFFFAOYSA-N 0.000 description 1
- WROKENRIDCHHQX-UHFFFAOYSA-N 3-[(3-fluoropyridin-2-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-2h-1,3-benzothiazin-4-one Chemical compound FC1=CC=CN=C1CN1C(=O)C2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2SC1 WROKENRIDCHHQX-UHFFFAOYSA-N 0.000 description 1
- BEJSXTRJVMOIMR-UHFFFAOYSA-N 3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-phenoxyphenyl)-1,2,3-benzotriazin-4-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=O)=N1 BEJSXTRJVMOIMR-UHFFFAOYSA-N 0.000 description 1
- NYPNRPBYHRJYDM-UHFFFAOYSA-N 3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 NYPNRPBYHRJYDM-UHFFFAOYSA-N 0.000 description 1
- MNFIKWZLBRHHKD-UHFFFAOYSA-N 3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]quinazolin-4-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3N=C2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MNFIKWZLBRHHKD-UHFFFAOYSA-N 0.000 description 1
- QTCQZAAPOJOGOF-UHFFFAOYSA-N 3-[(3-methyl-1,2-oxazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1N=C(C)C=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N=N1 QTCQZAAPOJOGOF-UHFFFAOYSA-N 0.000 description 1
- PCAZUJZXARNAFY-UHFFFAOYSA-N 3-[(3-phenyl-1,2-oxazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2ON=C(C=2)C=2C=CC=CC=2)C2=O)C2=C1 PCAZUJZXARNAFY-UHFFFAOYSA-N 0.000 description 1
- ULJSSYVRVJBHMT-UHFFFAOYSA-N 3-[(4,5-dimethyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=C(C)N=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N=N1 ULJSSYVRVJBHMT-UHFFFAOYSA-N 0.000 description 1
- UPQPUIZVSTYPLR-UHFFFAOYSA-N 3-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]quinazolin-4-one Chemical compound CC1=NON=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N=C1 UPQPUIZVSTYPLR-UHFFFAOYSA-N 0.000 description 1
- SNLPZDDWIJUFNT-UHFFFAOYSA-N 3-[(4-methyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound CC1=COC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 SNLPZDDWIJUFNT-UHFFFAOYSA-N 0.000 description 1
- RRCIGAXIILGNAX-UHFFFAOYSA-N 3-[(5-chloropyrimidin-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2N=CC(Cl)=CN=2)C2=O)C2=C1 RRCIGAXIILGNAX-UHFFFAOYSA-N 0.000 description 1
- QUSAWSOXNFAWOE-UHFFFAOYSA-N 3-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2N=C(ON=2)C2CC2)C2=O)C2=C1 QUSAWSOXNFAWOE-UHFFFAOYSA-N 0.000 description 1
- DSTZNWXQCBJZFV-UHFFFAOYSA-N 3-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2OC(=NN=2)C2CC2)C2=O)C2=C1 DSTZNWXQCBJZFV-UHFFFAOYSA-N 0.000 description 1
- QTVFTUCTLPOEOB-UHFFFAOYSA-N 3-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2SC(=NN=2)C2CC2)C2=O)C2=C1 QTVFTUCTLPOEOB-UHFFFAOYSA-N 0.000 description 1
- CNZFFNBXZXEYSN-UHFFFAOYSA-N 3-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=NC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CNZFFNBXZXEYSN-UHFFFAOYSA-N 0.000 description 1
- UYJBHSXSYYYBJI-UHFFFAOYSA-N 3-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]quinazolin-4-one Chemical compound O1C(C)=NC(CN2C(C3=CC(=CC=C3N=C2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 UYJBHSXSYYYBJI-UHFFFAOYSA-N 0.000 description 1
- OMIUBIHDDNDFIJ-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=CC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 OMIUBIHDDNDFIJ-UHFFFAOYSA-N 0.000 description 1
- OKQXGQUXXITFGU-UHFFFAOYSA-N 3-[(5-methyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound O1C(C)=CN=C1CN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N=N1 OKQXGQUXXITFGU-UHFFFAOYSA-N 0.000 description 1
- GODCHLOBELCOGH-UHFFFAOYSA-N 3-[(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC=2N=C(ON=2)C=2N=CC=CC=2)C2=O)C2=C1 GODCHLOBELCOGH-UHFFFAOYSA-N 0.000 description 1
- CAZOWGFYQRZXOI-UHFFFAOYSA-N 3-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound N1=NC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1C(C)C(ON=1)=NC=1C1CC1 CAZOWGFYQRZXOI-UHFFFAOYSA-N 0.000 description 1
- QSFSGEFPXVHKND-UHFFFAOYSA-N 3-[1-(3-pyrimidin-2-yl-1,2,4-oxadiazol-5-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound N1=NC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1C(C)C(ON=1)=NC=1C1=NC=CC=N1 QSFSGEFPXVHKND-UHFFFAOYSA-N 0.000 description 1
- CRLREFILVUROPV-UHFFFAOYSA-N 3-[2-[4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=C(C=CN=2)C=2N=C(ON=2)C2CC2)C2=O)C2=C1 CRLREFILVUROPV-UHFFFAOYSA-N 0.000 description 1
- ZLWYNMIRQBBVLO-UHFFFAOYSA-N 3-[2-oxo-2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC(=O)N2CCN(CC2)C=2N=CC=CN=2)C2=O)C2=C1 ZLWYNMIRQBBVLO-UHFFFAOYSA-N 0.000 description 1
- HTGNLKPXFJQUPN-UHFFFAOYSA-N 3-[[1-(hydroxymethyl)cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound N1=NC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC1(CO)CC1 HTGNLKPXFJQUPN-UHFFFAOYSA-N 0.000 description 1
- DJJRQTRZKOMSSL-UHFFFAOYSA-N 3-[[1-(imidazol-1-ylmethyl)cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC2(CN3C=NC=C3)CC2)C2=O)C2=C1 DJJRQTRZKOMSSL-UHFFFAOYSA-N 0.000 description 1
- XANGBZGURYFKGJ-UHFFFAOYSA-N 3-[[1-(morpholin-4-ylmethyl)cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC2(CN3CCOCC3)CC2)C2=O)C2=C1 XANGBZGURYFKGJ-UHFFFAOYSA-N 0.000 description 1
- SPXXECDYKZVAOM-UHFFFAOYSA-N 3-[[1-(pyrimidin-2-yloxymethyl)cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC2(COC=3N=CC=CN=3)CC2)C2=O)C2=C1 SPXXECDYKZVAOM-UHFFFAOYSA-N 0.000 description 1
- FUHROAJDLPVKNX-UHFFFAOYSA-N 3-[[1-(pyrrolidin-1-ylmethyl)cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CC2(CN3CCCC3)CC2)C2=O)C2=C1 FUHROAJDLPVKNX-UHFFFAOYSA-N 0.000 description 1
- LBPKSFAONAJFQR-UHFFFAOYSA-N 3-[[1-[(2-ethylimidazol-1-yl)methyl]cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound CCC1=NC=CN1CC1(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)CC1 LBPKSFAONAJFQR-UHFFFAOYSA-N 0.000 description 1
- CRACBDUCLOYEMI-UHFFFAOYSA-N 3-[[1-[(2-methylimidazol-1-yl)methyl]cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound CC1=NC=CN1CC1(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)CC1 CRACBDUCLOYEMI-UHFFFAOYSA-N 0.000 description 1
- CFTQQVMUZQXSHR-UHFFFAOYSA-N 3-[[1-[(3,5-dimethylpyrazol-1-yl)methyl]cyclopropyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound N1=C(C)C=C(C)N1CC1(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)CC1 CFTQQVMUZQXSHR-UHFFFAOYSA-N 0.000 description 1
- KZYOYSYESPSJEB-UHFFFAOYSA-N 3-piperidin-4-yl-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(C2CCNCC2)C2=O)C2=C1 KZYOYSYESPSJEB-UHFFFAOYSA-N 0.000 description 1
- IVZPTIYFMPFMFE-UHFFFAOYSA-N 6-(2-piperidin-1-ylpyrimidin-5-yl)-3-(2-pyrimidin-2-yloxyethyl)-1,2,3-benzotriazin-4-one Chemical compound N1=NC2=CC=C(C=3C=NC(=NC=3)N3CCCCC3)C=C2C(=O)N1CCOC1=NC=CC=N1 IVZPTIYFMPFMFE-UHFFFAOYSA-N 0.000 description 1
- SYWQTRAKSJADAU-UHFFFAOYSA-N 6-(4-cyclopropylphenyl)-3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-1,2,3-benzotriazin-4-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(=CC=2)C2CC2)=O)=N1 SYWQTRAKSJADAU-UHFFFAOYSA-N 0.000 description 1
- YWBREWILCXTOBV-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-3-(2-pyrazol-1-ylethyl)-1,2,3-benzotriazin-4-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C=2C=C3C(=O)N(CCN4N=CC=C4)N=NC3=CC=2)C=C1 YWBREWILCXTOBV-UHFFFAOYSA-N 0.000 description 1
- ZCPNVZDLYSYCNY-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-1,2,3-benzotriazin-4-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3N=N2)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=O)=N1 ZCPNVZDLYSYCNY-UHFFFAOYSA-N 0.000 description 1
- FBPYNRKZMQEMHM-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-3-[2-oxo-2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C=2C=C3C(=O)N(CC(=O)N4CCN(CC4)C=4N=CC=CN=4)N=NC3=CC=2)C=C1 FBPYNRKZMQEMHM-UHFFFAOYSA-N 0.000 description 1
- ZSEAIQWZTFIJQM-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-3-[2-[3-(trifluoromethyl)pyrazol-1-yl]ethyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCN2N=C(C=C2)C(F)(F)F)C2=O)C2=C1 ZSEAIQWZTFIJQM-UHFFFAOYSA-N 0.000 description 1
- JXBOVJLWPPHXJA-UHFFFAOYSA-N 7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline-2-carbaldehyde Chemical compound FC(C1=CC=C(C=C1)C1=CC=C2CCN(CC2=C1)C=O)(F)F JXBOVJLWPPHXJA-UHFFFAOYSA-N 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 description 1
- PXUREPXLWOVBRX-UHFFFAOYSA-N C1(CC1)C(=O)OCN1N=NC2=C(C1=O)C=C(C=C2)C1=CC=C(C=C1)OC(F)(F)F Chemical compound C1(CC1)C(=O)OCN1N=NC2=C(C1=O)C=C(C=C2)C1=CC=C(C=C1)OC(F)(F)F PXUREPXLWOVBRX-UHFFFAOYSA-N 0.000 description 1
- ZEIGRTIURXOKFK-UHFFFAOYSA-N CC(C(C1=O)=C(C=C2)N=NN1OCC1=NC=CC=N1)=C2C(C=C1)=CC=C1OC(F)(F)F Chemical compound CC(C(C1=O)=C(C=C2)N=NN1OCC1=NC=CC=N1)=C2C(C=C1)=CC=C1OC(F)(F)F ZEIGRTIURXOKFK-UHFFFAOYSA-N 0.000 description 1
- XHXXZEMPBRGNDW-UHFFFAOYSA-N CC(C)(C)C(C1=CC(C2=CC=C(C(F)(F)F)C=C2)=CC=C1CC1)N1C(C1=CN=NN1C1=CC=CC=C1)=O Chemical compound CC(C)(C)C(C1=CC(C2=CC=C(C(F)(F)F)C=C2)=CC=C1CC1)N1C(C1=CN=NN1C1=CC=CC=C1)=O XHXXZEMPBRGNDW-UHFFFAOYSA-N 0.000 description 1
- LZRMRRNTHMXVPV-UHFFFAOYSA-N CCC(CCC1)N1C(N1CC2=CC(C(C=C3)=CC=C3OC(F)(F)F)=CC=C2CC1)=O Chemical compound CCC(CCC1)N1C(N1CC2=CC(C(C=C3)=CC=C3OC(F)(F)F)=CC=C2CC1)=O LZRMRRNTHMXVPV-UHFFFAOYSA-N 0.000 description 1
- 206010007556 Cardiac failure acute Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022562 Intermittent claudication Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000007718 Stable Angina Diseases 0.000 description 1
- 208000008253 Systolic Heart Failure Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- SRBGTXQPSRHJMM-FQEVSTJZSA-N [(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound OC[C@@H]1CCCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 SRBGTXQPSRHJMM-FQEVSTJZSA-N 0.000 description 1
- OTKPMQHUPQVJFR-OAHLLOKOSA-N [(3r)-3-(hydroxymethyl)pyrrolidin-1-yl]-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1[C@H](CO)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OTKPMQHUPQVJFR-OAHLLOKOSA-N 0.000 description 1
- IONRUZWDNHQAGD-UHFFFAOYSA-N [3-(hydroxymethyl)azetidin-1-yl]-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1C(CO)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 IONRUZWDNHQAGD-UHFFFAOYSA-N 0.000 description 1
- QFWQKUIWTWSDKA-UHFFFAOYSA-N [7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]-(1,3,5-trimethylpyrazol-4-yl)methanone Chemical compound CC1=NN(C)C(C)=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 QFWQKUIWTWSDKA-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- HZMCBXVBPLTOOI-UHFFFAOYSA-N azetidin-1-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone N-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound N1=C(N=CC=C1)CNC(=O)N1CC2=CC(=CC=C2CC1)C1=CC=C(C=C1)C(F)(F)F.N1(CCC1)C(=O)N1CC2=CC(=CC=C2CC1)C1=CC=C(C=C1)C(F)(F)F HZMCBXVBPLTOOI-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000021156 intermittent vascular claudication Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- WSAPRCBVDRQBGK-UHFFFAOYSA-N n-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethoxy)phenyl]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)NCC=3N=CC=CN=3)C2=C1 WSAPRCBVDRQBGK-UHFFFAOYSA-N 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- QGLRQDBKALACJO-UHFFFAOYSA-N pyridazin-3-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3N=NC=CC=3)C2=C1 QGLRQDBKALACJO-UHFFFAOYSA-N 0.000 description 1
- AMGSWILVROFFCD-UHFFFAOYSA-N pyrimidin-2-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3N=CC=CN=3)C2=C1 AMGSWILVROFFCD-UHFFFAOYSA-N 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161484500P | 2011-05-10 | 2011-05-10 | |
| US61/484,500 | 2011-05-10 | ||
| US201161503543P | 2011-06-30 | 2011-06-30 | |
| US61/503,543 | 2011-06-30 | ||
| PCT/US2012/036976 WO2012154760A1 (en) | 2011-05-10 | 2012-05-08 | Fused heterocyclic compounds as sodium channel modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014517833A JP2014517833A (ja) | 2014-07-24 |
| JP2014517833A5 true JP2014517833A5 (enrdf_load_stackoverflow) | 2015-06-25 |
| JP5934787B2 JP5934787B2 (ja) | 2016-06-15 |
Family
ID=46147042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510414A Expired - Fee Related JP5934787B2 (ja) | 2011-05-10 | 2012-05-08 | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
Country Status (21)
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SMT201700456T1 (it) * | 2009-07-27 | 2017-11-15 | Gilead Sciences Inc | Composti eterociclici fusi come modulatori dei canali ionici |
| CA2802288C (en) | 2010-07-02 | 2018-08-21 | Gilead Sciences, Inc. | Triazolopyridinone compounds as ion channel modulators |
| CN105693645B (zh) * | 2011-05-10 | 2018-10-09 | 吉利德科学公司 | 作为离子通道调节剂的稠合杂环化合物 |
| NO3175985T3 (enrdf_load_stackoverflow) | 2011-07-01 | 2018-04-28 | ||
| UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| US20150045305A1 (en) | 2012-01-27 | 2015-02-12 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR102365651B1 (ko) | 2013-10-04 | 2022-02-21 | 인피니티 파마슈티칼스, 인코포레이티드 | 헤테로사이클릭 화합물 및 그의 용도 |
| US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG11201604457XA (en) * | 2013-12-19 | 2016-07-28 | Gilead Sciences Inc | Fused heterocyclic compounds as ion channel modulators |
| CA2943075C (en) | 2014-03-19 | 2023-02-28 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| US9617226B2 (en) | 2014-09-05 | 2017-04-11 | AbbVie Deutschland GmbH & Co. KG | Fused heterocyclic or carbocyclic compounds carrying a substituted cycloaliphatic radical and use thereof for treating vasopressin-related diseases |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| CN104530037B (zh) * | 2015-01-21 | 2020-12-18 | 华东理工大学 | 一种具有杀线虫活性的三嗪杂环化合物及其制法和用途 |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| HK1260897A1 (zh) | 2015-08-21 | 2019-12-27 | Portola Pharmaceuticals, Inc. | 使用四氢异喹啉小分子来结合并调节pcsk9的蛋白活性的组合物和方法 |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| EP3350183B1 (en) | 2015-09-14 | 2025-04-02 | Twelve Therapeutics, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| BR112018005637B1 (pt) | 2015-09-23 | 2023-11-28 | Janssen Pharmaceutica Nv | Compostos derivados de quinoxalina, quinolina e quinazolinona,composições farmacêuticas que os compreende, e uso dos referidos compostos |
| DK3353164T3 (da) | 2015-09-23 | 2022-01-24 | Janssen Pharmaceutica Nv | Bi-heteroarylsubstituerede 1,4-benzodiazepiner og anvendelser deraf til behandling af cancer |
| US10973825B2 (en) | 2015-12-09 | 2021-04-13 | Cadent Therapeutics, Inc. | Thienopyrimidinone NMDA receptor modulators and uses thereof |
| PT3386591T (pt) | 2015-12-09 | 2020-10-01 | Cadent Therapeutics Inc | Moduladores de recetores nmda heteroaromáticos e suas utilizações |
| WO2017147328A1 (en) | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2018098491A1 (en) | 2016-11-28 | 2018-05-31 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| DK3548033T3 (da) | 2016-11-28 | 2024-07-15 | Praxis Prec Medicines Inc | Forbindelser og deres fremgangsmåde til anvendelse |
| CA3047403A1 (en) | 2016-12-22 | 2018-06-28 | Cadent Therapeutics, Inc. | Nmda receptor modulators and uses thereof |
| WO2018148745A1 (en) | 2017-02-13 | 2018-08-16 | Praxis Precision Medicines , Inc. | Compounds and their methods of use |
| US10266542B2 (en) | 2017-03-15 | 2019-04-23 | Mirati Therapeutics, Inc. | EZH2 inhibitors |
| WO2018187480A1 (en) | 2017-04-04 | 2018-10-11 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| BR112019026478A2 (pt) * | 2017-06-14 | 2020-07-14 | Trevena, Inc. | compostos para modulação da atividade de s1p1 e métodos de uso dos mesmos |
| US11278535B2 (en) | 2017-08-15 | 2022-03-22 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| BR112020015583B1 (pt) | 2018-01-31 | 2022-12-06 | Mirati Therapeutics, Inc | Composto, composição farmacêutica e seu uso para tratar câncer |
| CN108276352B (zh) * | 2018-03-13 | 2022-09-20 | 华东理工大学 | 一种具有杀线虫活性的含氮杂环化合物及其制法和用途 |
| TWI831786B (zh) | 2018-05-30 | 2024-02-11 | 美商普雷西斯精密藥品公司 | 離子通道調節劑 |
| SG11202101125VA (en) | 2018-08-03 | 2021-03-30 | Cadent Therapeutics Inc | Heteroaromatic nmda receptor modulators and uses thereof |
| KR102288434B1 (ko) * | 2018-10-18 | 2021-08-12 | 에이치케이이노엔 주식회사 | 신규한 (이소프로필-트리아졸릴)피리디닐 치환된 벤조옥사지논 또는 벤조티아지논 유도체 및 이의 용도 |
| US11773099B2 (en) | 2019-05-28 | 2023-10-03 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| US11279700B2 (en) | 2019-05-31 | 2022-03-22 | Praxis Precision Medicines, Inc. | Ion channel modulators |
| US11505554B2 (en) | 2019-05-31 | 2022-11-22 | Praxis Precision Medicines, Inc. | Substituted pyridines as ion channel modulators |
| US12252493B2 (en) | 2019-06-05 | 2025-03-18 | Mirati Therapeutics, Inc. | Imidazo[1,2-c]pyrimidine derivatives as PRC2 inhibitors for treating cancer |
| WO2021026672A1 (en) | 2019-08-09 | 2021-02-18 | Novartis Ag | Heterocyclic wdr5 inhibitors as anti-cancer compounds |
| WO2021046183A1 (en) * | 2019-09-05 | 2021-03-11 | Trevena, Inc. | Methods of treating epilepsy using the same |
| CA3158600A1 (en) | 2019-11-19 | 2021-05-27 | Brian H. Heasley | Compounds and methods of preparing compounds s1p1 modulators |
| US11767325B2 (en) | 2019-11-26 | 2023-09-26 | Praxis Precision Medicines, Inc. | Substituted [1,2,4]triazolo[4,3-a]pyrazines as ion channel modulators |
| WO2022047260A1 (en) * | 2020-08-28 | 2022-03-03 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| CN116265444B (zh) * | 2021-12-16 | 2025-09-05 | 华东理工大学 | 杀线虫活性的化合物及其制备方法和用途 |
Family Cites Families (220)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2867616A (en) | 1950-05-17 | 1959-01-06 | Syntex Sa | 7-dehydro diosgenin compounds and process for making same |
| US2867618A (en) * | 1957-02-14 | 1959-01-06 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazine |
| US2826575A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | 3, 3'-alkylenebis |
| NL128591C (enrdf_load_stackoverflow) | 1965-07-02 | |||
| US3441649A (en) | 1966-08-18 | 1969-04-29 | Univ Minnesota | Suppression of cardiac ventricular fibrillation and cardiac arrhythmias with bretylium tosylate |
| US3594372A (en) | 1968-08-13 | 1971-07-20 | American Home Prod | Pyrimido(4,5-e)(1,4)oxazepin-5-ones and derivatives thereof |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4062881A (en) | 1974-07-26 | 1977-12-13 | Cincinnati Milacron Chemicals, Inc. | Sulfide containing tin stabilizers |
| US4230705A (en) | 1976-09-22 | 1980-10-28 | American Cyanamid Company | 6-Phenyl-1,2,4-triazolo[4,3-b]pyridazines and their uses in treating anxiety |
| US4242515A (en) | 1979-03-28 | 1980-12-30 | American Cyanamid Company | Substituted 3-alkyl-6-phenyl-1,2,4-triazolo-[4,3-a]pyridines |
| US4244953A (en) | 1979-10-24 | 1981-01-13 | American Cyanamid Company | Substituted 6-phenyl-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyridines |
| JPS5675428A (en) | 1979-11-21 | 1981-06-22 | Ayanori Takabe | Hypoglycemic agent containing procainamide hydrochloride |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US4812565A (en) | 1982-09-30 | 1989-03-14 | A. H. Robins Company, Incorporated | Fused aromatic oxazepinones, thiazepinones, diazepinones and sulfur analogs thereof |
| US5364620A (en) | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| US4665181A (en) * | 1984-05-17 | 1987-05-12 | Pennwalt Corporation | Anti-inflammatory phthalazinones |
| US4654343A (en) | 1985-10-31 | 1987-03-31 | American Cyanamid Company | N-substituted-N[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4746655A (en) | 1987-06-10 | 1988-05-24 | A. H. Robins Company, Incorporated | Fused aromatic-spiropiperidine oxazepinones(and thiones) |
| US5001139A (en) | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| US4992445A (en) | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US4902514A (en) | 1988-07-21 | 1990-02-20 | Alza Corporation | Dosage form for administering nilvadipine for treating cardiovascular symptoms |
| JPH061779Y2 (ja) | 1989-11-13 | 1994-01-19 | 株式会社新潟鐵工所 | 合成樹脂成形機におけるホッパー下部の冷却水装置 |
| DE4010488A1 (de) | 1990-03-31 | 1991-10-02 | Hoechst Ag | Benzoxazinderivate, verfahren zu ihrer herstellung und ihre verwendung zum behandeln oder zur prophylaxe von krankheiten |
| CA2044564A1 (en) | 1990-06-28 | 1991-12-29 | Quirico Branca | Amino acid derivatives |
| CN1060467A (zh) | 1990-09-25 | 1992-04-22 | 武田药品工业株式会社 | 1，3-苯并嗪衍生物、其生产方法和用途 |
| JPH04209692A (ja) | 1990-12-03 | 1992-07-31 | Asahi Glass Co Ltd | フォトクロミック材料 |
| US5246948A (en) | 1991-05-10 | 1993-09-21 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| US5939412A (en) | 1992-06-26 | 1999-08-17 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| WO1993000095A2 (en) | 1991-06-28 | 1993-01-07 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| US5674863A (en) | 1991-10-18 | 1997-10-07 | Genentech, Inc. | Nonpeptidyl integrin inhibitors having specificity for the GPIIb IIIa receptor |
| US5250679A (en) | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
| US5272158A (en) | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH061779A (ja) | 1992-02-06 | 1994-01-11 | Wakamoto Pharmaceut Co Ltd | ベンズオキサジノン誘導体 |
| JPH06107647A (ja) | 1992-08-12 | 1994-04-19 | Takeda Chem Ind Ltd | １，３−ベンゾオキサジン誘導体の製造法 |
| US5442055A (en) | 1992-11-13 | 1995-08-15 | Tanabe Seiyaku Co., Ltd. | Azetidinone compound and process for preparation thereof |
| US6011150A (en) | 1992-11-13 | 2000-01-04 | Tanabe Seiyaku Co., Ltd. | Azetidinone compound and process for preparation thereof |
| GB9225860D0 (en) | 1992-12-11 | 1993-02-03 | Smithkline Beecham Plc | Novel treatment |
| GB9226302D0 (en) | 1992-12-17 | 1993-02-10 | Smithkline Beecham Plc | Pharmaceuticals |
| US5550229A (en) | 1993-06-23 | 1996-08-27 | Tanabe Seiyaku Co., Ltd. | Alkylation process for preparing azetidinone compound and starting compound therefor |
| DE19526173A1 (de) | 1995-07-18 | 1997-01-30 | Hoechst Ag | Polyfullerenaddukte, Verfahren zu ihrer regioselektiven Herstellung und deren Verwendung |
| JPH09157262A (ja) | 1995-12-08 | 1997-06-17 | Tanabe Seiyaku Co Ltd | アゼチジノン誘導体及びその合成中間体の製法 |
| US5773186A (en) | 1996-02-19 | 1998-06-30 | Fuji Photo Film Co., Ltd. | Heat-sensitive recording material |
| GB9619492D0 (en) | 1996-09-18 | 1996-10-30 | Smithkline Beecham Plc | Novel treatment |
| WO1998047885A1 (en) | 1997-04-18 | 1998-10-29 | Smithkline Beecham Plc | A bicyclic aryl or a bicyclic heterocyclic ring containing compounds having a combined 5ht1a, 5ht1b and 5ht1d receptor antagonistic activity |
| WO1998054135A1 (fr) * | 1997-05-30 | 1998-12-03 | Meiji Seika Kaisha, Ltd. | Composes heterocycliques azotes et medicament contre l'hyperlipemie en contenant |
| JP3964053B2 (ja) | 1997-07-10 | 2007-08-22 | 三井化学株式会社 | 遷移金属化合物からなるオレフィン重合用触媒ならびに重合方法 |
| CA2300906A1 (en) | 1997-09-08 | 1999-03-18 | Unilever Plc | Method for enhancing the activity of an enzyme |
| HRP20000492A2 (en) | 1998-01-21 | 2000-12-31 | Merck Sharp & Dohme | Triazolo-pyridazine derivatives as ligands for gaba receptors |
| WO1999041246A1 (en) | 1998-02-11 | 1999-08-19 | Du Pont Pharmaceuticals Company | Novel cyclic sulfonamide derivatives as metalloproteinase inhibitors |
| WO1999042456A2 (en) | 1998-02-18 | 1999-08-26 | Neurosearch A/S | Novel compounds and their use as positive ampa receptor modulators |
| AU755855B2 (en) | 1998-06-16 | 2002-12-19 | Merck Sharp & Dohme Limited | Triazolo-pyridine derivatives as ligands for GABA receptors |
| JP2002527520A (ja) | 1998-10-21 | 2002-08-27 | ノボ ノルディスク アクティーゼルスカブ | 新規化合物、その製造及び使用 |
| BR0009650A (pt) | 1999-04-09 | 2002-01-02 | Meiji Seika Kaisha | Composto, composição farmacêutica, processos para inibir a secreção de uma lipoproteìna contendo apolipoproteìna b, para inibir a biossìntese de triglicerìdeos e para prevenir ou tratar hiperlipidemia, doenças arterioscleróticas e pancreatite, e, uso do composto |
| CA2373073A1 (en) * | 1999-05-07 | 2000-11-16 | Takeda Chemical Industries, Ltd. | Cyclic compounds and uses thereof |
| JP2003508588A (ja) | 1999-08-27 | 2003-03-04 | ザ、プロクター、エンド、ギャンブル、カンパニー | 陽イオン系処方成分を使用する、色に対して安全な洗濯方法 |
| WO2001016274A1 (en) | 1999-08-27 | 2001-03-08 | The Procter & Gamble Company | Stable formulation components, compositions and laundry methods employing same |
| EP1206518A1 (en) | 1999-08-27 | 2002-05-22 | The Procter & Gamble Company | Color safe laundry methods employing zwitterionic formulation components |
| AU6935800A (en) | 1999-08-27 | 2001-03-26 | Procter & Gamble Company, The | Controlled availability of formulation components, compositions and laundry methods employing same |
| BR0013616B1 (pt) | 1999-08-27 | 2011-12-27 | composiÇço de alvejamento e composto catalisador orgÂnico de lavanderia. | |
| ATE327978T1 (de) | 1999-08-27 | 2006-06-15 | Procter & Gamble | Bleichverstärkende verbindungen, zusammensetzungen und waschverfahren |
| WO2001016275A1 (en) | 1999-08-27 | 2001-03-08 | The Procter & Gamble Company | Fast-acting formulation components, compositions and laundry methods employing same |
| JP2003533525A (ja) | 2000-05-15 | 2003-11-11 | ダーウィン・ディスカバリー・リミテッド | Ｍｍｐおよびｔｎｆ阻害活性を有するヒドロキサム酸およびカルボン酸誘導体 |
| JP4982937B2 (ja) | 2000-08-01 | 2012-07-25 | 小野薬品工業株式会社 | ３，４−ジヒドロイソキノリン誘導体化合物及びその化合物を有効成分とする薬剤 |
| US20040058915A1 (en) | 2000-08-29 | 2004-03-25 | Khanna Ish Kumar | Compounds containing a bicyclic ring system useful as alpha v beta 3 antagonists |
| JP2002205992A (ja) | 2000-11-08 | 2002-07-23 | Takeda Chem Ind Ltd | 二環式トリアゾロン誘導体およびそれを含有する除草剤 |
| EP1354602B1 (en) | 2000-12-26 | 2006-10-04 | Sankyo Company, Limited | Medicinal compositions containing diuretic and insulin resistance-improving agent |
| AP2002002463A0 (en) | 2001-03-09 | 2002-06-30 | Pfizer Prod Inc | Novel triazolo-pyrimides anti-inflammatory compounds. |
| US6998408B2 (en) | 2001-03-23 | 2006-02-14 | Bristol-Myers Squibb Pharma Company | 6-5, 6-6, or 6-7 Heterobicycles as factor Xa inhibitors |
| US20030114448A1 (en) | 2001-05-31 | 2003-06-19 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| JP2005089298A (ja) | 2001-09-18 | 2005-04-07 | Japan Tobacco Inc | ナフタレン化合物及びその医薬用途 |
| TW200300347A (en) | 2001-11-13 | 2003-06-01 | Schering Corp | Nk1 antagonists |
| US7196108B2 (en) | 2002-03-08 | 2007-03-27 | Incyte San Diego Inc. | Bicyclic heterocycles for the treatment of diabetes and other diseases |
| JP2003277384A (ja) | 2002-03-26 | 2003-10-02 | Kyorin Pharmaceut Co Ltd | 縮合ニ環式ピリジン誘導体 |
| JP2003321461A (ja) | 2002-04-25 | 2003-11-11 | Kyorin Pharmaceut Co Ltd | 縮合ビフェニル誘導体 |
| BR0313724A (pt) | 2002-08-13 | 2005-06-28 | Warner Lambert Co | Derivados de azaisoquinolina como inibidores de metaloproteinase de matriz |
| JP2005539020A (ja) * | 2002-08-13 | 2005-12-22 | ワーナー−ランバート カンパニー リミティド ライアビリティー カンパニー | マトリクスメタロプロテイナーゼ阻害物質としてのクロモン誘導体 |
| DE10238865A1 (de) | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US20040242572A1 (en) * | 2002-08-24 | 2004-12-02 | Boehringer Ingelheim International Gmbh | New carboxamide compounds having melanin concentrating hormone antagonistic activity, pharmaceutical preparations comprising these compounds and process for their manufacture |
| PA8579601A1 (es) | 2002-08-30 | 2004-05-07 | Pfizer Prod Inc | Compuestos antiinflamatorios de di y trifloruro-triazolo-piridinas |
| US7005523B2 (en) | 2002-08-30 | 2006-02-28 | Pfizer Inc. | Cycloalkyl-[4-(trifluorophenyl)-oxazol-5yl]-triazolo-pyridines |
| WO2004026292A1 (ja) | 2002-09-20 | 2004-04-01 | Tsumura & Co. | 鎮咳薬 |
| US20040204404A1 (en) | 2002-09-30 | 2004-10-14 | Robert Zelle | Human N-type calcium channel blockers |
| GB0223730D0 (en) | 2002-10-11 | 2002-11-20 | Novartis Ag | Organic compounds |
| AU2003294235A1 (en) | 2002-10-22 | 2004-05-13 | The Trustees Of The University Of Pennsylvania | Fragments and activity of rel protein in m. tuberculosis adn other uses thereof |
| WO2004043940A1 (en) | 2002-11-07 | 2004-05-27 | Merck & Co., Inc. | Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| CN100430386C (zh) | 2002-11-07 | 2008-11-05 | 默克公司 | 苯丙氨酸衍生物作为二肽基肽酶抑制剂用于治疗或预防糖尿病 |
| MXPA05007389A (es) | 2003-01-13 | 2006-02-10 | Cortex Pharma Inc | Metodo para el tratamiento de la deficiencia cognitiva debido a la privacion de sueno y estres. |
| JP4209692B2 (ja) | 2003-01-28 | 2009-01-14 | 株式会社日立製作所 | 図書管理システム及び書誌情報管理方法 |
| AR044503A1 (es) | 2003-03-18 | 2005-09-14 | Merck & Co Inc | Triazoles sustituidos con biarilo como bloqueantes del canal de sodio |
| DE10317526A1 (de) | 2003-04-16 | 2004-11-04 | Degussa Ag | Verfahren zum Delignifizieren von ligninhaltigen Faserstoffen |
| AU2004232939A1 (en) * | 2003-04-17 | 2004-11-04 | Merck Sharp & Dohme Corp. | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
| US20060264496A1 (en) | 2003-04-25 | 2006-11-23 | H. Lundbeck A/S | Substituted indoline and indole derivatives |
| WO2004101509A2 (en) | 2003-05-06 | 2004-11-25 | Case Western Reserve University | Functionalized benzoxazines, polymers and copolymers thereof |
| AU2004253543B2 (en) | 2003-07-01 | 2009-02-19 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| AU2004260624A1 (en) | 2003-07-21 | 2005-02-10 | Solvay Pharmaceuticals Gmbh | Use of 3,7-diazabicyclo`3, 3,1 !nonane compounds for the treatment and/or prophylaxis of anti-arrhythmic events in male human patients |
| ATE548358T1 (de) | 2003-08-05 | 2012-03-15 | Vertex Pharma | Tetrahydrochinazolin-verbindungen als inhibitoren von spannungsabhängigen ionenkanälen |
| US20050239767A1 (en) | 2003-10-28 | 2005-10-27 | Chan Michael K | Intermolecular SNAr of the heterocycle-activated nitro and fluoro groups-application in the synthesis of polyazamacrocyclic ligands |
| MXPA06007023A (es) | 2003-12-18 | 2006-08-31 | Pfizer Prod Inc | Metodos para tratar la inflamacion aguda en animales con inhibidores de p38 map cinasa. |
| PT1731512E (pt) | 2004-03-05 | 2014-11-24 | Nissan Chemical Ind Ltd | Composto de benzamida substituída com isoxazolina e agente de controlo de organismos nocivos |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| GB0412986D0 (en) | 2004-06-10 | 2004-07-14 | Xention Discovery Ltd | Compounds |
| WO2006002470A1 (en) | 2004-06-30 | 2006-01-12 | Monash University | Chiral ligands for asymmetric catalysis |
| JP2006063064A (ja) | 2004-07-27 | 2006-03-09 | Takeda Chem Ind Ltd | 受容体作動剤 |
| JP2007297283A (ja) | 2004-07-28 | 2007-11-15 | Santen Pharmaceut Co Ltd | 新規桂皮酸関連化合物 |
| WO2006020959A2 (en) | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
| US7521457B2 (en) | 2004-08-20 | 2009-04-21 | Boehringer Ingelheim International Gmbh | Pyrimidines as PLK inhibitors |
| EP1784188B1 (en) | 2004-08-23 | 2010-07-14 | Merck Sharp & Dohme Corp. | Fused triazole derivatives as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes |
| AU2005285083B2 (en) | 2004-09-13 | 2011-03-10 | Merck Sharp & Dohme Corp. | Tricyclic anilide spirohydantoin CGRP receptor antagonists |
| AR050948A1 (es) | 2004-09-24 | 2006-12-06 | Hoffmann La Roche | Derivados de ftalazinona; su obtencion y su utilizacion en la fabricacion de medicamentos para el tratamiento del cancer. |
| WO2006048727A1 (en) * | 2004-11-02 | 2006-05-11 | Pfizer Products Inc. | Piperazinylphenalkyl lactam/amine ligands for the 5ht1b receptor |
| WO2006091897A2 (en) | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Derivatives of 8-substituted xanthines |
| CN101258134B (zh) * | 2005-03-11 | 2011-10-12 | 欧加农股份有限公司 | 2-(4-氧代-4h-喹唑啉-3-基)乙酰胺衍生物及其作为加压素v3拮抗剂的用途 |
| TW200643015A (en) * | 2005-03-11 | 2006-12-16 | Akzo Nobel Nv | 2-(4-oxo-4H-quinazolin-3-yl)acetamide derivatives |
| US20080176830A1 (en) | 2005-04-14 | 2008-07-24 | Adams Nicholas D | Compounds, Compositions, and Methods |
| AR056317A1 (es) | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| JP5794721B2 (ja) | 2005-05-17 | 2015-10-14 | サーコード バイオサイエンス インコーポレイテッド | 眼障害の治療のための組成物および方法 |
| TW200714597A (en) | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| JP2008543867A (ja) | 2005-06-17 | 2008-12-04 | ワイス | セロトニン阻害剤ならびに５−ｈｔ１ａアゴニストおよびアンタゴニストとして有用な三環系化合物 |
| TW200726765A (en) | 2005-06-17 | 2007-07-16 | Bristol Myers Squibb Co | Triazolopyridine cannabinoid receptor 1 antagonists |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| WO2007004028A2 (en) | 2005-06-30 | 2007-01-11 | Ranbaxy Laboratories Limited | Processes for the preparation of penems and its intermediate |
| WO2007023750A1 (ja) | 2005-08-26 | 2007-03-01 | National University Corporation University Of Toyama | 乾燥羊膜及び羊膜の乾燥処理方法 |
| CA2621255A1 (en) | 2005-09-21 | 2007-04-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| CA2623026A1 (en) | 2005-09-23 | 2007-04-05 | Schering Corporation | Fused tetracyclic mglur1 antagonists as therapeutic agents |
| WO2007047604A2 (en) | 2005-10-18 | 2007-04-26 | Elixir Pharmaceuticals, Inc. | Sirt1 inhibition |
| TW200804290A (en) | 2005-11-15 | 2008-01-16 | Astrazeneca Ab | Compounds and uses thereof |
| EP1954268B1 (en) | 2005-11-18 | 2012-09-26 | Merck Sharp & Dohme Corp. | Spirolactam bicyclic cgrp receptor antagonists |
| CA2629409A1 (en) | 2005-11-18 | 2007-05-31 | Merck & Co., Inc. | Spirolactam aryl cgrp receptor antagonists |
| TW200734342A (en) | 2005-12-15 | 2007-09-16 | Astrazeneca Ab | New compounds for the treatment of cardiac arrhythmias |
| CN101330914A (zh) | 2005-12-16 | 2008-12-24 | 爱尔康公司 | 使用alk5调节剂控制眼内压 |
| US8013073B2 (en) | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
| US8097617B2 (en) | 2006-03-31 | 2012-01-17 | Novartis Ag | Organic compounds |
| EP2742936A1 (en) | 2006-05-16 | 2014-06-18 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| JP2009539988A (ja) | 2006-06-12 | 2009-11-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャネルの調節因子として有用なチエノピリミジン |
| WO2008005338A1 (en) | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| CN101541783B (zh) | 2006-06-30 | 2014-10-01 | 苏尼西斯制药有限公司 | 吡啶酮基pdk1抑制剂 |
| US20090318412A1 (en) | 2006-07-11 | 2009-12-24 | Takahiro Matsumoto | Tricyclic heterocyclic compound and use thereof |
| EP2046788A1 (en) | 2006-07-12 | 2009-04-15 | Syngeta Participations AG | Triazolopyridine derivatives as herbicides |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| MEP5909A (en) * | 2006-08-22 | 2011-12-20 | Matrix metalloproteinase inhibitors | |
| US7790741B2 (en) | 2006-10-06 | 2010-09-07 | Abbott Laboratories | Imidazothiazoles and imidazoxazoles |
| WO2008118141A2 (en) | 2006-10-17 | 2008-10-02 | Acadia Pharmaceuticals Inc. | Use of cannabinoid modulating compounds in combination with other therapeutic compounds for adjunctive therapy |
| CL2007003049A1 (es) | 2006-10-23 | 2008-05-16 | Cephalon Inc Pharmacopeia Drug | Compuestos derivados de 2,4-diaminopirimidina; composicion farmaceutica, utiles para tratar trastornos proliferativos. |
| SI2343286T1 (sl) | 2006-10-28 | 2015-05-29 | Methylgene Inc. | Derivati dibenzo(b,f)(1,4) oksazepina kot inhibitorji histonske deacetilaze |
| WO2008053913A1 (fr) * | 2006-11-02 | 2008-05-08 | Shionogi & Co., Ltd. | Dérivé de sulfonylurée capable d'inhiber sélectivement mmp-13 |
| CA2670651A1 (en) | 2006-12-21 | 2008-07-03 | Cv Therapeutics, Inc. | Reduction of cardiovascular symptoms |
| US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
| WO2008094909A2 (en) * | 2007-01-29 | 2008-08-07 | Xenon Pharmaceuticals Inc. | Quinazolinone and fused pyrimidinone compounds and their use in treating sodium channel-mediated diseases or conditions |
| EP2131657A1 (en) | 2007-02-28 | 2009-12-16 | Merck & Co., Inc. | Substituted benzodiazepinones, benzoxazepinones and benzothiazepinones as sodium channel blockers |
| US8247403B2 (en) | 2007-03-07 | 2012-08-21 | Takeda Pharmaceutical Company Limited | Benzoxazepine derivatives and use thereof |
| GB0706072D0 (en) | 2007-03-28 | 2007-05-09 | Sterix Ltd | Compound |
| KR20100015685A (ko) | 2007-04-12 | 2010-02-12 | 씨브이 쎄러퓨틱스, 인코포레이티드 | 인슐린 분비 강화를 위한 라놀라진 |
| WO2008134553A1 (en) | 2007-04-26 | 2008-11-06 | Xenon Pharmaceuticals Inc. | Methods of using bicyclic compounds in treating sodium channel-mediated diseases |
| WO2008144483A2 (en) | 2007-05-18 | 2008-11-27 | Armgo Pharma, Inc. | Agents for treating disorders involving modulation of ryanodine receptors |
| EP2170337A4 (en) | 2007-06-28 | 2013-12-18 | Abbvie Inc | NEW TRIAZOLOPYRIDAZINE |
| US20090012103A1 (en) | 2007-07-05 | 2009-01-08 | Matthew Abelman | Substituted heterocyclic compounds |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| WO2009026444A1 (en) | 2007-08-22 | 2009-02-26 | President And Fellows Of Harvard College | Ryanodine channel binders and uses thereof |
| CN101848896A (zh) * | 2007-09-12 | 2010-09-29 | 惠氏有限责任公司 | 作为组胺-3拮抗剂的异喹啉基和异吲哚啉基衍生物 |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| JP5710268B2 (ja) | 2007-12-19 | 2015-04-30 | ジェネンテック， インコーポレイテッド | ８−アニリノイミダゾピリジン及びその抗ガン及び／又は抗炎症剤としての使用 |
| PE20091339A1 (es) | 2007-12-21 | 2009-09-26 | Glaxo Group Ltd | Derivados de oxadiazol con actividad sobre receptores s1p1 |
| WO2009089027A1 (en) | 2008-01-09 | 2009-07-16 | Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Service, National Institutes Of Health | Phosphodiesterase inhibitors |
| KR20110013348A (ko) | 2008-02-06 | 2011-02-09 | 길리애드 사이언시즈, 인코포레이티드 | 통증 치료를 위한 라놀라진의 용도 |
| KR20100124262A (ko) | 2008-02-13 | 2010-11-26 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 비시클로아민 유도체 |
| JP2009286773A (ja) | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
| US20110288070A1 (en) | 2008-05-05 | 2011-11-24 | ROGERS Kathryn | Methods for treating cognitive disorders using inhibitors of histone deacetylase |
| WO2009137499A1 (en) | 2008-05-05 | 2009-11-12 | Envivo Pharmaceuticals, Inc. | Inhibitors of histone deacetylase |
| DE102008024182A1 (de) | 2008-05-19 | 2009-11-26 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtung |
| JP2011522818A (ja) | 2008-06-06 | 2011-08-04 | アボット・ラボラトリーズ | 新規１，２，４オキサジアゾール化合物およびこれらの使用方法 |
| KR101695501B1 (ko) | 2008-06-17 | 2017-01-11 | 아스트라제네카 아베 | 피리딘 화합물 |
| EP2307027A4 (en) | 2008-07-11 | 2012-08-15 | Neumedics | TETRACYCLINE DERIVATIVES WITH REDUCED ANTIBIOTIC ACTIVITY AND NEUROPROTECTIVE PROPERTIES |
| JP5303561B2 (ja) | 2008-08-12 | 2013-10-02 | 日本曹達株式会社 | 含窒素ヘテロ環誘導体および農園芸用殺菌剤 |
| US20110190511A1 (en) | 2008-08-18 | 2011-08-04 | Im&T Research, Inc. | Methods For Preparing Fluoroalkyl Arylsulfinyl Compounds And Fluorinated Compounds Thereto |
| CA2735653A1 (en) | 2008-09-04 | 2010-03-11 | Gilead Sciences, Inc. | Method of treating atrial fibrillation |
| US20100113461A1 (en) | 2008-10-29 | 2010-05-06 | Gilead Palo Alto, Inc. | Substituted heterocyclic compounds |
| WO2010056527A2 (en) | 2008-10-30 | 2010-05-20 | Gilead Palo Alto, Inc. | Fused heterocyclic compounds as ion channel modulators |
| US20100113514A1 (en) | 2008-10-30 | 2010-05-06 | Gilead Palo Alto, Inc. | Fused heterocyclic compounds as ion channel modulators |
| WO2010056865A1 (en) | 2008-11-14 | 2010-05-20 | Gilead Palo Alto, Inc. | Quinoline derivatives as ion channel modulators |
| WO2010068461A1 (en) | 2008-11-25 | 2010-06-17 | Gilead Palo Alto, Inc. | Co-administration of ranolazine and cardiac glycosides |
| CN102292338B (zh) | 2008-12-08 | 2016-09-28 | 萌蒂制药国际有限公司 | 酪氨酸激酶蛋白受体拮抗剂 |
| CA2746221A1 (en) | 2008-12-08 | 2010-07-08 | Sirtris Pharmaceuticals, Inc. | Isoindolinone and related analogs as sirtuin modulators |
| JP5271069B2 (ja) | 2008-12-24 | 2013-08-21 | 三和シヤッター工業株式会社 | 開閉装置 |
| FR2943342B1 (fr) | 2009-03-20 | 2011-03-04 | Servier Lab | Nouveaux derives de benzothiadiazepines,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US9150554B2 (en) | 2009-03-27 | 2015-10-06 | Presidio Pharmaceuticals, Inc. | Fused ring inhibitors of hepatitis C |
| US20100305093A1 (en) | 2009-04-09 | 2010-12-02 | Exelixis, Inc. | Inhibitors of mTOR and Methods of Making and Using |
| SMT201700456T1 (it) | 2009-07-27 | 2017-11-15 | Gilead Sciences Inc | Composti eterociclici fusi come modulatori dei canali ionici |
| BR112012006807A2 (pt) | 2009-09-28 | 2020-11-03 | F.Hoffmann-La Roche Ag | compostos da fórmula i, composição farmacêutica, composta por composto, método de tratamento de câncer em um mamífero, uso de um composto, kit para tratar um condição mediada por pi3k e processo para a preparação de um composto |
| WO2011042920A1 (en) | 2009-10-07 | 2011-04-14 | Decode Genetics Ehf | Genetic variants indicative of vascular conditions |
| WO2011056985A2 (en) | 2009-11-04 | 2011-05-12 | Gilead Sciences, Inc. | Substituted heterocyclic compounds |
| WO2011075607A1 (en) | 2009-12-18 | 2011-06-23 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| TWI508726B (zh) | 2009-12-21 | 2015-11-21 | Gilead Sciences Inc | 治療心房纖維性顫動之方法 |
| CA2802288C (en) | 2010-07-02 | 2018-08-21 | Gilead Sciences, Inc. | Triazolopyridinone compounds as ion channel modulators |
| WO2012019076A1 (en) | 2010-08-06 | 2012-02-09 | The Trustees Of Columbia University In The City Of New York | Compositions and methods for preventing and treating cardiac ischemia/reperfusion injury |
| WO2012019071A1 (en) | 2010-08-06 | 2012-02-09 | The Trustees Of Columbia University In The City Of New York | Methods of preventing and treating sarcopenia |
| WO2012037105A1 (en) | 2010-09-14 | 2012-03-22 | The Trustees Of Columbia University In The City Of New York | Methods of treating, ameliorating or preventing stress-induced neuronal disorders and diseases |
| WO2012036233A1 (ja) * | 2010-09-17 | 2012-03-22 | 塩野義製薬株式会社 | メラニン凝集ホルモン受容体アンタゴニスト活性を有する縮合へテロ環誘導体 |
| UY33618A (es) | 2010-09-21 | 2012-03-30 | Purdue Pharma Lp | Analogos de buprenorfina |
| US8999967B2 (en) | 2010-09-29 | 2015-04-07 | Presidio Pharmaceuticals, Inc. | Tricyclic fused ring inhibitors of hepatitis C |
| US20140378436A9 (en) | 2010-11-24 | 2014-12-25 | Exelixis, Inc. | Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their use and Manufacture |
| JP5675428B2 (ja) | 2011-02-25 | 2015-02-25 | サンドビック株式会社 | ベルトプレス装置 |
| WO2012126901A1 (en) | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| CN105693645B (zh) | 2011-05-10 | 2018-10-09 | 吉利德科学公司 | 作为离子通道调节剂的稠合杂环化合物 |
| EP2714011B1 (en) | 2011-06-03 | 2018-01-31 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long qt syndrome and potassium delayed-rectifier current |
| ES2598027T3 (es) | 2011-07-01 | 2017-01-24 | Bayer Intellectual Property Gmbh | Pirrolotriazinas sustituidas con hidroximetilarilo como inhibidores de ALK1 |
| NO3175985T3 (enrdf_load_stackoverflow) | 2011-07-01 | 2018-04-28 | ||
| UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| HK1200114A1 (en) | 2011-09-21 | 2015-07-31 | Gilead Sciences, Inc. | Sodium channel blockers reduce glucagon secretion |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| US8623860B2 (en) | 2011-12-30 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Azetidine derivatives, pharmaceutical compositions and uses thereof |
| US20150045305A1 (en) | 2012-01-27 | 2015-02-12 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| US8969588B2 (en) | 2012-06-05 | 2015-03-03 | Gilead Pharmasset Llc | Solid forms of an antiviral compound |
| ES2805341T3 (es) | 2012-06-13 | 2021-02-11 | Acesion Pharma Aps | Composiciones farmacéuticas para terapia de combinación |
| WO2014134419A1 (en) | 2013-03-01 | 2014-09-04 | Gilead Sciences, Inc. | Use of ikach blockers for the treatment of cardiac diseases |
| CN104844535A (zh) | 2014-02-13 | 2015-08-19 | 吉利德科学公司 | 用于制备稠合杂环离子通道调节剂的方法 |
| TW201613908A (en) | 2014-02-13 | 2016-04-16 | Gilead Sciences Inc | Solid forms of an ion channel modulator |
-
2012
- 2012-05-08 CN CN201610186640.5A patent/CN105693645B/zh not_active Expired - Fee Related
- 2012-05-08 PT PT127225951T patent/PT2707361T/pt unknown
- 2012-05-08 ES ES12722595.1T patent/ES2648820T3/es active Active
- 2012-05-08 NZ NZ617987A patent/NZ617987A/en not_active IP Right Cessation
- 2012-05-08 PL PL12722595T patent/PL2707361T3/pl unknown
- 2012-05-08 US US13/466,995 patent/US9115096B2/en active Active
- 2012-05-08 CA CA2834164A patent/CA2834164A1/en not_active Abandoned
- 2012-05-08 TW TW104130125A patent/TWI577670B/zh not_active IP Right Cessation
- 2012-05-08 CN CN201280030042.9A patent/CN103649056B/zh not_active Expired - Fee Related
- 2012-05-08 AU AU2012253653A patent/AU2012253653A1/en not_active Abandoned
- 2012-05-08 JP JP2014510414A patent/JP5934787B2/ja not_active Expired - Fee Related
- 2012-05-08 SI SI201231122T patent/SI2707361T1/sl unknown
- 2012-05-08 WO PCT/US2012/036976 patent/WO2012154760A1/en active Application Filing
- 2012-05-08 TW TW101116359A patent/TWI510480B/zh not_active IP Right Cessation
- 2012-05-08 NZ NZ716420A patent/NZ716420A/en not_active IP Right Cessation
- 2012-05-08 EP EP17187226.0A patent/EP3275870B1/en active Active
- 2012-05-08 ES ES17187226T patent/ES2785475T3/es active Active
- 2012-05-08 MX MX2013012798A patent/MX361350B/es active IP Right Grant
- 2012-05-08 EP EP12722595.1A patent/EP2707361B1/en active Active
- 2012-05-08 BR BR112013028886A patent/BR112013028886A2/pt not_active IP Right Cessation
- 2012-05-08 KR KR1020137031829A patent/KR20140033377A/ko not_active Abandoned
- 2012-05-08 EA EA201391532A patent/EA028156B9/ru not_active IP Right Cessation
- 2012-05-09 AR ARP120101626 patent/AR086319A1/es unknown
- 2012-05-09 UY UY34062A patent/UY34062A/es not_active Application Discontinuation
-
2013
- 2013-10-24 IL IL229045A patent/IL229045A0/en unknown
-
2015
- 2015-07-24 US US14/808,296 patent/US9403782B2/en active Active
-
2016
- 2016-04-21 AU AU2016202535A patent/AU2016202535B2/en not_active Ceased
- 2016-06-21 US US15/188,701 patent/US9682998B2/en active Active
- 2016-12-19 HK HK16114404.3A patent/HK1238627A1/zh unknown
-
2018
- 2018-07-19 HK HK18109345.3A patent/HK1249902A1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014517833A5 (enrdf_load_stackoverflow) | ||
| AU2012356374B2 (en) | Pyridinone and pyrimidinone derivatives as factor XIa inhibitors | |
| RU2329261C2 (ru) | Новое 2-гетероарил-замещенное производное бензимидазола | |
| JP6130964B2 (ja) | Ａｐｊ受容体のトリアゾールアゴニスト | |
| TWI358409B (en) | Heteroaryl substituted piperidine derivatives | |
| JP5036316B2 (ja) | アリールオキシ置換ベンズイミダゾール誘導体 | |
| US20190119210A1 (en) | Aromatic sulfonamide derivatives | |
| TWI583683B (zh) | 雜芳香環甲基環狀胺衍生物 | |
| EP2298747B1 (en) | Triazole derivative or salt thereof | |
| JP2013535423A5 (enrdf_load_stackoverflow) | ||
| WO2011148922A1 (ja) | 新規キナゾリン化合物 | |
| JP2011503166A5 (enrdf_load_stackoverflow) | ||
| JP2017512794A5 (enrdf_load_stackoverflow) | ||
| JPWO2006109846A1 (ja) | トリアゾール誘導体およびその用途 | |
| JP2014521651A (ja) | 特定のキヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 | |
| JP2010505809A5 (enrdf_load_stackoverflow) | ||
| JP2019511466A (ja) | オレキシン受容体調節因子としてのハロ置換ピペリジン | |
| KR20120108963A (ko) | 스핑고신-1-포스페이트 수용체 효능제 | |
| JPWO2021124172A5 (enrdf_load_stackoverflow) | ||
| TW201341381A (zh) | Ｎ－取代吡唑衍生物 | |
| HK1116180A (en) | Aryloxy-substituted benzimidazole derivatives | |
| HK1217200A1 (zh) | 抗病毒化合物 |